Palladium catalysis in reductive alkyl group transfer from trialkylamines to nitroarenes followed by cyclization

被引：8

作者：

Cho, Chan Sik ^{[1
]}

Kim, Tae Gyun ^{[1
]}

Kim, Hae Won ^{[2
]}

机构：

[1] Kyungpook Natl Univ, Dept Appl Chem, Taegu 702701, South Korea

[2] Kyungil Univ, Dept Display & Chem Engn, Kyungsan 712701, South Korea

来源：

CATALYSIS COMMUNICATIONS | 2009年 / 10卷 / 11期

关键词：

Alkyl group transfer; Cyclization; Nitroarenes; Palladium catalyst; Quinolines; Trialkylamines; FRIEDLANDER QUINOLINE SYNTHESIS; ONE-POT SYNTHESIS; 2-AMINOBENZYL ALCOHOL; N-HETEROCYCLIZATION; KETONES; COMPLEX; DERIVATIVES; CHLORIDES; ANILINES;

D O I：

10.1016/j.catcom.2009.03.024

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Nitroarenes having electron donating and withdrawing substituents are reductively cyclized with an array of trialkylamines in the presence of a catalytic amount of Pd/C along with tin(II) chloride at 120 degrees C in a toluene/H(2)O medium to afford quinolines in moderate to good yields. The product yield depends on the position of the substituent of nitroarenes and the chain length of trialkylamines. The addition of tin(II) chloride is essential for the formation of quinolines and toluene/H(2)O is the solvent of choice. (C) 2009 Elsevier B. V. All rights reserved.

引用

页码：1482 / 1485

页数：4

共 21 条

[1] TRANSITION-METAL COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION - SYNTHESIS OF 4(3H)-QUINAZOLINONE DERIVATIVES FROM N-(2-NITROBENZOYL)AMIDES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :310-312

[2] PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3375-3380

[3] Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines [J].

Amii, H ;

Kishikawa, Y ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (08) :1109-1112

[4] A new green approach to the Friedlander synthesis of quinolines [J].

Arcadi, A ;

Chiarini, M ;

Di Giuseppe, S ;

Marinelli, F .

SYNLETT, 2003, (02) :203-206

[5] A recyclable palladium-catalyzed modified Friedlander quinoline synthesis [J].

Cho, Chan Sik ;

Ren, Wen Xiu .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (19) :4182-4186

[6] An approach for quinolines via palladium-catalyzed Heck coupling followed by cyclization [J].

Cho, Chan Sik ;

Kim, Jun Uk .

TETRAHEDRON LETTERS, 2007, 48 (22) :3775-3778

[7] A copper(II)-catalyzed protocol for modified Friedlander quinoline synthesis [J].

Cho, Chan Sik ;

Ren, Wen Xiu ;

Shim, Sang Chul .

TETRAHEDRON LETTERS, 2006, 47 (38) :6781-6785

[8] Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization [J].

Cho, CS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (17) :4094-4097

[9] Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis [J].

Cho, CS ;

Kim, BT ;

Kim, TJ ;

Shim, SC .

CHEMICAL COMMUNICATIONS, 2001, (24) :2576-2577

[10] Ruthenium-catalyzed reductive cyclization of nitroarenes with trialkylamines leading to quinolines [J].

Cho, CS ;

Kim, TK ;

Kim, BT ;

Kim, TJ ;

Shim, SC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 650 (1-2) :65-68

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